Water → HCID 12822512, compound

HRID 980309Notes

Reaction equation

HRID 980309 reaction equation
CI.CN([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=2)[NH:9][CH:8]=1)C.[C-:22]#[N:23].[K+].O>CS(C)=O>[C:22]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][NH:17][S:18]([CH3:21])(=[O:19])=[O:20])[CH:14]=2)[NH:9][CH:8]=1)#[N:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 9032Potassium CyanideHCID 20222399HCID 20222399, compound

Product 1

HCID 12822512HCID 12822512, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Methyl iodide (0.15 ml) was added to a stirred solution of N-[[3-[(dimethylamino)methyl]-1H-indol-5-yl]methyl]methanesulphonamide (0.5 g) in dimethyl sulphoxide (20 ml) followed by potassium cyanide (0.3 g) and the resulting solution stirred for 2 h, before pouring it into water (80 ml) and extracting with ethyl acetate (2×30 ml). The combined organic extracts were washed with water (30 ml), hydrochloric acid (2N, 30 ml) dried (Na2SO4) and evaporated to dryness to give a fawn foam which was purified on a silica column (kieselgel 60, 10 g) eluted with ethyl acetate to give the title compound as a white solid (0.08 g) m.p. 106°-9° after crystallisation from ethyl acetate.

Workup

  1. extractionextracting with ethyl acetate (2×30 ml)
  2. washThe combined organic extracts were washed with water (30 ml), hydrochloric acid (2N, 30 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated to dryness
  5. customto give a fawn foam which
  6. customwas purified on a silica column (kieselgel 60, 10 g)
  7. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-ee5f72d091934bcd8ed837e4e0d47ec5
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

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